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Total synthesis of incarviditone and incarvilleatone
Patrick D Brown1, Anthony C Willis, Michael S Sherburn
1Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
Abstract:
The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.
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